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Free porn pictures 10 25 50 100 150 results per page   Search for: Filter by: Any size Small Medium Large Huge Anytime Today This week This month  Gallery Name   Images   Quality   Added    horny af 🥵    8   2025-06-17  sweetbumhole <443 fans>   Femdom Feminization Captions 1 (Chastity, Petplay, Pegging)    10   2025-06-16  Femdom feminization captions, no maledom. cha0self <361 fans>   SISSY GIF'S CAPTIONS-86    12   2025-06-16  kparc1212 <4,773 fans>   Advanced Cuck Ideas    24   2025-06-16  Here are more caps for you all coldsoup <353 fans>   AlwaysCuteSissyCaptions    52   2025-06-16  NOT MINE! I just wanted to share some of my favorite captions by AlwayCute. PLEASE SUPPORT THEM at... tumblr.com/alwayscute ... deviantart.com/alwayscutetumblr ... S_Millie <110 fans>   Sissy Slut Sarah Simone ~ Dildo Sucking Training    4   2025-06-16  GoodGirlBambi <613 fans>   Sissy Slut Sarah Simone ~ Owned by SissyMaster2022    1   2025-06-16  GoodGirlBambi <613 fans>   Sissy Slut Sarah Simone ~ Task Completed    5   2025-06-16  Sissymaster2022 set me a task to announce that I am now his property. I was ordered to caption 5 of my photos to tell everyone. GoodGirlBambi <613 fans>   Just Heels    41   2025-06-16  Ich bin eine devote Schlampe, möchte ordentlich und Hemmungslos durchgefickt werden. Kein Küssen. Ich blase aktiv, passiv möchte ich das nicht!!! Diskretion, Sauberkeit, Gesundheit ist ein absolutes muss.- Ich bin nicht besuchbar, gerne Outdoor, bei... MarieNudeman <338 fans>   Femboys and Trans Gurls    33   2025-06-16  TsApril <128 fans>   Sissy Slut Sarah Simone ~ Now the Property of SissyMaster2022    5   2025-06-16  I was instructed by my new Master (sissymaster2022) to caption three photos of myself stating that I am now his property. He already has an insurance policy on me to keep me inline. GoodGirlBambi <613 fans>   Betasafe Censored Pornstars 11    100   2025-06-15  Censored pornstars for betasafe sissy bois. Jerk off to feet, high heels and bbc, loser. Simp to pixels of women and transsexuals that real men get to look at all the time. wesmantooth <782 fans>   HOT GIF 1123    12   2025-06-15  samir50 <1,853 fans>   Sissy Captions - The Bully 2    41   2025-06-15  Sissy Captions Sissy_Scarlett <1,437 fans>   Sissy maid :3😼    10   2025-06-15  1 Betalincel <110 fans>   Big Butt Sissy Bimbo    8   2025-06-15  Sissy Anraya22 <22 fans>   Fantastic marriage    17   2025-06-15  Openurlegs <3,413 fans>   Yes honey we can share the big beautiful black cock    27   2025-06-15  Openurlegs <3,413 fans>   Captions-Interracial Sissy GIF's- Every White Boys Fantasy 15     16   2025-06-15  kparc1212 <4,773 fans>   S    12   2025-06-15  sissymaster202 <815 fans>   My stroke buddy 1    9   2025-06-15  Cute stories from my 'straight' friend, with whom I like to hang out and watch porn together. Annalena20 <123 fans>   Sissy Sarah Simone    35   2025-06-15  sissymaster202 <815 fans>   It's not gay if... 2    9   2025-06-15  It's not gay, so just push it inside me :)nnCaptions that are so relatable for me daily Annalena20 <123 fans>   Sissy Slut Sarah Simone ~ Riding her Dildo on Webcam    14   2025-06-15  Putting a face to the masked webcam videos of myself riding my dildo for strangers online. GoodGirlBambi <613 fans>   Gallery_196_My_sissy_style_pink_shorts_8    3   2025-06-15  Pictures of me, please comment freefriki <339 fans>   Sissy Slut Sarah Simone ~ Posing in her Pink Nightie     10   2025-06-15  GoodGirlBambi <613 fans>   Older Me, Always a Sissy Faggot    5   2025-06-15  earlier years of sissy faggot tami. A Master I chatted with online made these tshirts, sent them to me, and had me take photos in them. Perfect for exposure and humiliation tamis_demise <135 fans>   Sissy Trine getting pussy fucked    11   2025-06-15  Sissy Trine fucked by pink sissy machine.I have a video of this too. As a sissy I am public property. Repost me anywhere you want. trisette1 <841 fans>   Sissy Slut Sarah Simone ~ Dumb Whore    5   2025-06-15  Sissy Slut Sarah Simone is a dumb whore. GoodGirlBambi <613 fans>   More pics I like    32   2025-06-15  sissymaster202 <815 fans>   Sissy Hanna    30   2025-06-15  sissymaster202 <815 fans>   German Sissy Jacqueline Feet Mix No. 3    104   2025-06-15  For my Feet-Fans, my stinkers bare or in nylon, flats, buffalo or sneakers, in many situations. At work, freetime, in and outdoor, as gurl or normal, cuckold situations and many more...nHave fun and commend your favorites please.nKisses Jacqueline German Tranny <4,389 fans>   Stupid Instagram Filter Porn    31   2025-06-15  A silly sissy showing girly side with Snapchat filters. Rile-Rile <85 fans>   Animated Sissy GIF Captions 21 (Mommy's boy)    9   2025-06-15  Deviant mothers use their feminine wiles to guide their helpless sons into sissyhood. shysteffie <331 fans>   It's not gay if...    9   2025-06-14  What if your stroke buddy invites you for a movie and it turns out he wants your ass? Not gay! Or if your friend wants to test condoms? Not gay! Explore some scenarios with me, of which some I have already experienced myself! Annalena20 <123 fans>   Straight Porn 3    9   2025-06-14  It can't be gay, it is with girls right? Annalena20 <123 fans>   Sultry Night Adventures    144   2025-06-14  Lorena4u <647 fans>   Sissy, Premature, and Loser memes concerning Dr. Sissy Michelle    4   2025-06-14  SamiSSIpresi <70 fans>   Sissy in black playing with her cock until she cums    9   2025-06-14  lido_up_2 <143 fans>   Captions for every flavor     150   2025-06-14  Captions of things I like, I'm not the creator, nor do I profit from them. If you own them or are in them and want them down, dm me the link to the one you want deleted and I will asap! .. They are just fantasy! More to come WebSlutExposer <263 fans>   Seren new caps 339    12   2025-06-14  APRIL 2023. I have started to post a new set of captions, created almost entirely on smartphone, using face, photography and text apps. All the 'base' pics are from legal sites/sources (18 plus). The face swaps are either celebs/pornstars from readily... SerenPidyn <1,235 fans>   Captions: Sissy, Cuckold, Ballbusting, Domination 61    22   2025-06-14  Some of these I made, some of them I got from you guys, some of them I saw on-line and wanted to change something, like fix a typo. I hope you enjoy them; they are in this file it is because I did! redbird2991 <1,659 fans>   Sissy sophie totally out of control    28   2025-06-14  Sophieprettypo <253 fans>   The happy sissy cuckold 01    24   2025-06-14  Sissies love to wear gorgeous lingerie, but they also crave to be dominated and/or humiliated by their sexually liberal wives and their alpha-male lovers LongstockingsM <859 fans>   Sissy Sarah Danielle Simone ~ Formerly Sarah Tidmarsh     14   2025-06-14  Captions made by other men when I was still named Sarah Tidmarsh. The Sissy Hunter changed my name. GoodGirlBambi <613 fans>   Shiny Heel Collection - One of My Favorite Artists    121   2025-06-14  On of my all time favorite artists... just a small collection. jawanaut <1,711 fans>   Bad Bully Captions 9: Sissified by Bully 2    16   2025-06-14  Even more mean-spirited bully captions, beta boys bested by bullies and messed up mentally by maniacal moms, their sexuality subverted to sissy status as the weakling wimps are forcibly feminized into tormented trannies and sex-hungry she-males. ViennaSheraton <1,367 fans>   Aline Travestie (796)    20   2025-06-14  Aline travestie en lingerie aline_trav <1,458 fans>   RL In Blue    55   2025-06-14  raelynn98 <262 fans>   SydneySinns - tribute me     7   2025-06-13  A few new. A few not so new. All meant for you to cum to. I like my makeup to be just right. So it looks better when there's cum all over my face ;p SydneySinns <344 fans>   Jiz Makes Me Gag But They Make Me Swallow! Sissy Captions    24   2025-06-13  Fake tits, branded with a vile epithet. They’ve transformed you from straight male into seemingly willing sissy whore… Just like in my e-books, available only at www.lulu.com/spotlight/candy_runt Candy_Runt <4,614 fans>   AoA - Vile Villagers: Part 9 [Sissy, Captions, AI]    10   2025-06-13  Adventures of Alexa - Sissy Caption Stories. AI-Images by Lorena4u. AlexaRider2517 <191 fans>   Blackmailer Said to Dress Like a Sissy Whore, So I Did    24   2025-06-13  FORCED FEMINIZATION AND SISSY HUMILIATION STORIES. Cum celebrate the world of forced feminization and public sissy humiliation with me and my full-length e-books! Available exclusively online at www.lulu.com/spotlight/candy_runt Candy_Runt <4,614 fans>   You cuck I cuck we all cuck    15   2025-06-13  Openurlegs <3,413 fans>   German Sissy cosplaying Misty    17   2025-06-13  Dressing up as Misty and also in a shiny tight Pikachu "Bunny" Suit ;-) Alice8989 <115 fans>   Sissy Captions 61    40   2025-06-13  Sissy Captions Sissy_Scarlett <1,437 fans>   Sissy Sasha exposed    9   2025-06-13  Sasha_Cool <470 fans>   i need a gentle, soft daddy🫣    8   2025-06-13  sweetbumhole <443 fans>   lick me clean 👅     6   2025-06-13  sweetbumhole <443 fans>   i am back✌️    7   2025-06-13  sweetbumhole <443 fans>   Pink string thong 2    4   2025-06-13  Nikki-Suss <81 fans>   Sissy Julie Allison Dress: Black Ruched Mini    25   2025-06-13  Sissy Julie Allison Dress: Black Ruched Mini Dress JulieAllison <607 fans>   Caged sissy    3   2025-06-13  Rode my toys today and liked these photos feel free to dm me! Sortedsissy <39 fans>   Hot Femboy Sissy Needs an ass full of cum    21   2025-06-13  I hope you like my photos, help me publish them anywhere I like to exposure I leave personal info at the end or in my profile DaisySophie <267 fans>   Straight Porn 2    10   2025-06-12  It's not gay to watch straight porn, right? It is also not gay to take it up the ass if you are wearing femme clothes. Annalena20 <123 fans>   Sexy Trans Women 2    71   2025-06-12  DErnest <716 fans>   Sexy Trans Women 1    66   2025-06-12  DErnest <716 fans>   AoA - Vile Villagers: Part 8 [Sissy, Captions, AI]    9   2025-06-12  Adventures of Alexa - Sissy Caption Stories. AI-Images by Lorena4u. AlexaRider2517 <191 fans>   Andrea is a pretty feminized sissy    16   2025-06-12  Needing exposure as a woman greatlegs <1,025 fans>   Cracker Bitch Forced to Serve it&rsquo;s Black Master - sissy ca    24   2025-06-12  You didn't have a racist bone in your skinny little body, at least not until Rocco and his friends decided to make you their little sissy sex kitten. Now you've usually got a least one racist boner somewhere in your feminized body! - - - If you... Candy_Runt <4,614 fans>   tiny blue thong    24   2025-06-12  colinori <109 fans>   Psychologists who treat pathetic losers 25    24   2025-06-12  They say admitting it is the first step to recovery, only there's no recovery for you. Dominant female psychologists don't suffer pathetic, sissy, bitches. Dominant psychologists prefer not to waste their valuable time on beta wimps like you. They are... krista024 <2,905 fans>   Pink string thong    3   2025-06-12  Nikki-Suss <81 fans>   Sissy Sasha Sissy Jane Sissy Hanna    9   2025-06-12  1st 3 are Sissy Hanna 2nd 3 are Sissy Sasha 3rd 3 are Sissy Jane sissymaster202 <815 fans>   Sissy Slut Sarah Simone ~ Cock Craving GIFs    8   2025-06-12  Cock Craving GIFs. I have had this cock before. Yummy!!! GoodGirlBambi <613 fans>   My life as a castrated sissy whore(4): Beyond    30   2025-06-12  And like all stories, good or bad, mine comes to an end. I hope my experience helps you avoid making the same mistakes. It's too late for me, for several reasons that will become clear after you finish viewing this gallery, but perhaps my story will... sissystraight6 <2,550 fans>   Bound, Gagged, Sissy Faggot Bitch Forced to Accept Her Fate    4   2025-06-12  Bound, immobilized, feminized sissy faggot awaiting the arrival of the REAL MEN that arranged her training party for her coming out. tamis_demise <135 fans>   Twisted captions of Yami vol. 125    63   2025-06-12  whole lotta diaper tf this time yami_joeys_dog <1,042 fans>   Wigless, Outed, Exposed, Humiliated Feminized Sissy FAGGOT    6   2025-06-12  It's high time that photos were posted of an obviously feminized sissy faggot. Yet another sissy faggot that was meant to be trained into a completely obedient sissy bitch trained and owned by ALL REAL MEN. Blackmail material? Exposed, displayed.... tamis_demise <135 fans>   Sissy Faggot Maid Humiliation    10   2025-06-11  tamis_demise <135 fans>   More pictures I enjoy     82   2025-06-11  sissymaster202 <815 fans>   Straight Porn 1    9   2025-06-11  This is totally straight porn, right? Annalena20 <123 fans>   Advanced Cuck Ideas    24   2025-06-11  Hope you like coldsoup <353 fans>   Exposure of Sissies (with consent)    91   2025-06-11  My sissy friends ask me if i can exposed. Here. davidasissy <672 fans>   Sissy Playtime    14   2025-06-11  Cloe_Cockmunch <116 fans>   RL In White    12   2025-06-11  raelynn98 <262 fans>   Pix that stir my baby gravy - Take 6    32   2025-06-10  Yet again- a delicious assortment of images that can titillate and titivate your nether regions! EmkayH <1,800 fans>   Sissy Choices    37   2025-06-10  Sissy Choices Sissy_Scarlett <1,437 fans>   Vintage trans/shemale/sissys/gurls - varying quality    116   2025-06-10  These images are from good quality to bad, some are screen shot bad but I thought that they looked hot. This was a request from Amber in LV. chewchilla <1,342 fans>   I want to be your pregnant sissy faggot bride    72   2025-06-10  I decided to run some of my pics through AI with a prompt "I want to be a pregnant sissy bride standing near my husband"nWould love to read your comments whether you like it or not TransOksana <5,150 fans>   SHINY ASS DESTROYED BY A THICK PROLAPSE DILDO - Alisya JC    19   2025-06-10  With my shiny, oiled-up ass on full display, I can’t resist playing with my new thick prolapse dildo. Dressed in a tiny white hoodie and sheer black stockings, I stretch my hole wide, teasing every inch as the textured toy glides deep inside me.... alisyajc <2,024 fans>   You're Nothing But a Loser 132    24   2025-06-10  This gallery is intended to tap into the insecurities that a loser has, especially those involving his abilities when it comes to women. The reason you're here is because you're nothing but a loser. krista024 <2,905 fans>   TG/Sissy Captions #10    6   2025-06-10  Check out more on my DeviantArt~ Lexi221 <146 fans>   RL In Skirt    11  -  2025-06-10  raelynn98 <262 fans>   RL In Jeans    31   2025-06-10  raelynn98 <262 fans>   RL In Black    7   2025-06-10  raelynn98 <262 fans>   Submissive Sissy Captions 2    40   2025-06-09  Submissive Sissy Captions Sissy_Scarlett <1,437 fans>   Sissy Captions 06    7   2025-06-09  moki <345 fans>   Vicky sissy pink 2    22   2025-06-09  Got some new pink lingerie and thought i would share with you all, though at my age and this body i cant do it justice but i try., please comment if you want and be kind or dirty 😁 vicky_vicks <351 fans>   Femboy Brothers    8   2025-06-09  Femboys who are grateful they have understanding brothers. jonblacker <5,974 fans>   in panty    17   2025-06-09  dressman <1,489 fans>   SISSY GIF'S CAPTIONS-85    12   2025-06-09  kparc1212 <4,773 fans>   German Sissy Jacqueline Feet Mix No.1    60   2025-06-09  For my Feet-Fans, my stinkers bare or in nylon, flats, buffalo or sneakers, in many situations. At work, freetime, in and outdoor, as gurl or normal, cuckold situations and many more...nHave fun and commend your favorites please.nKisses Jacqueline German Tranny <4,389 fans>   Aline Travestie (795)    20   2025-06-09  Aline travestie en lingerie et en cage aline_trav <1,458 fans>   Femdom Captions 71    4   2025-06-08  clthong2 <555 fans>   Sissy Emily Demure - 080625    23   2025-06-08  New heels. 🤭💕💘 SissyEmilyDemu <24 fans>   Sissy Captions 60    40   2025-06-08  Sissy Captions Sissy_Scarlett <1,437 fans>   In my undies    8   2025-06-08  BrianPL100 <9 fans>   Sissy Cocksucker POV    31   2025-06-08  Get ready Sissy...time to suck cock for your creamy reward! HandPussyLover <806 fans>   Little Sissy with a Little Booty 4 captions     9   2025-06-08  Feel free to use ANY of our pictures 4 Captions 🥰 Sissyytboi <332 fans>   Daddy Holiday 2    168   2025-06-08  Lorena4u <647 fans>   Cloe - Sissy Schoolgirl    6   2025-06-08  Locked and plugged sissy schoolgirl waiting for a cock to suck on. Cloe_Cockmunch <116 fans>   Emily Demure - 070625    13   2025-06-07  SissyEmilyDemu <24 fans>   HOT GIF 1119    26   2025-06-07  samir50 <1,853 fans>   Today's outfits    16   2025-06-07  nylon cock <1,488 fans>   Slutty Black Lace Lingerie    246   2025-06-07  Snuskis80 <144 fans>   Sissy milking her cock    7   2025-06-07  lido_up_2 <143 fans>   Sissy Julie Allison Swimwear: Blue Slingshot Bikini    39   2025-06-07  Sissy Julie Allison Swimwear: Blue Slingshot Thong Bikini JulieAllison <607 fans>   Daddy Holiday    149   2025-06-07  Lorena4u <647 fans>   Sissy diary_5    100   2025-06-07  I've collected these images from various sources, including Imagefap. They illustrate my feelings towards femininity, and are also a source of inspiration for my queer transition as a nonbinary transfemme. Enjoy them! ❤ WreckedWhore <120 fans>   Taken from videos I&rsquo;ve made     52   2025-06-07  Undressing,getting hard,dripping cum,dresses your going to want to check this one out Charmstheshell <246 fans>   I have sucked this guy off too many times!     13   2025-06-07  He lets me dress for a quick blowjob that gets him off. I’ve got him off every single time without a problem . Charmstheshell <246 fans>   Gallery_195_My_hairy_cock_and_jeeerk_3    2   2025-06-07  Pictures of me, please comment freefriki <339 fans>   Gallery_194_My_sissy_style_pink_shorts_7    2   2025-06-07  Pictures of me, please comment freefriki <339 fans>   I'm nothing but a loser to Emmy Rossum    5   2025-06-07  Emmy is a perfect princess...to her, im lower than dog shit emmawatsonssla <2,360 fans>   Glorious Maids to emulate     139   2025-06-06  Serendipityxx <1,308 fans>   Black Lace Friday    130   2025-06-06  Snuskis80 <144 fans>   Doctor with a naughty sissy side    6   2025-06-06  SamiSSIpresi <70 fans>   Beta boi blackmailed to become his bitch - sissy captions    24   2025-06-06  Why did she hate me so much? What had I ever done to her to make me get dressed and madeup to look like a total whore, before forcing me to dance, real intimately, with all those horrible men at that disgusting club! And how could she just look on... Candy_Runt <4,614 fans>   Femdom Sissy Sluts    85   2025-06-06  Femdom sissy strapon pegging, CBT, spitroast, cock milking images. Mike32174 <536 fans>   Sissy In Pink Chastity Cage    235   2025-06-06  Snuskis80 <144 fans>   sissy goals and inspirations 12    26   2025-06-06  A collection of bodies and people I am jealous of and want to be, and situations and fantasies I'd love to experience one day. bbwsissyboi <111 fans>   Sissy Slut Sarah Simone ~ Addicted to Sissy Hypno     25   2025-06-06  Sissy hypnosis made Sarah Simone the slut she is today. GoodGirlBambi <613 fans>   Seren new caps 338    12   2025-06-06  APRIL 2023. I have started to post a new set of captions, created almost entirely on smartphone, using face, photography and text apps. All the 'base' pics are from legal sites/sources (18 plus). The face swaps are either celebs/pornstars from readily... SerenPidyn <1,235 fans>   Susanne's wonderful husband, Jens the faggot (reblog)    10   2025-06-06  Susanne's wonderful husband. Write how you would use him in front of his wife Filu <1,583 fans>   Gallery_193_My_sissy_style_pink_shorts_6    2   2025-06-06  Pictures of me, please comment freefriki <339 fans>   A few pictures I enjoy     30   2025-06-06  sissymaster202 <815 fans>   Submissive Sissy Captions 1    40   2025-06-05  Sissy Captions Sissy_Scarlett <1,437 fans>   Hooked Sissy    134   2025-06-05  Snuskis80 <144 fans>   Me Cindy Cross crossdressing in pink and white    4   2025-06-05  Me Cindy Cross crossdressing in pink and white. cindy_cross39 <1,668 fans>   Cuckold Life Twenty    23   2025-06-05  Enjoy your cuckold life! jillian_silver <313 fans>   Sissy got a new dress    8   2025-06-05  Got a new dress and some new cockrings so I just had to have a wank wearing them knifty764 <620 fans>   Sissies in Bondage - Zara Du Rose Special    12   2025-06-05  KarinaClarkeTV <829 fans>   Sissy Slut Sarah Simone ~ Slut for Life    19   2025-06-05  Sarah Simone ~ Sissy Slut for Life GoodGirlBambi <613 fans>   Sissy Slut Sarah Simone ~ Lace Body Stocking    5   2025-06-05  Lace body stockings make you feel like a proper sex doll. GoodGirlBambi <613 fans>   Sissy Slut Sarah Simone ~ Post Body Wax     5   2025-06-05  All good sissy sluts wax their entire body. Smooth and silky skin for hairy alpha males. GoodGirlBambi <613 fans>   Sissy Slut Sarah Simone ~ Plugged and Caged    7   2025-06-05  Sissy Slut Sarah Simone is always plugged and caged. GoodGirlBambi <613 fans>   Sissy 9     20   2025-06-04  Just a collection of sexy sissys KarinaClarkeTV <829 fans>   Masked fetish sissy    6   2025-06-04  PVClvr <262 fans>   My edit - 03.06.25    8   2025-06-04  Piceditor <310 fans> :: prev :: | 1 | ... | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | :: next ::